Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 133, Issue 19, Pages 7328-7331Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja2020873
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Funding
- National Institutes of Health [GM033049]
- National Science Foundation
- Stanford University
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Pd-catalyzed asymmetric prenylation of oxindoles to afford selectively either the prenyl or reverse-prenyl product has been demonstrated. Control of the regioselectivity in this transformation is governed by the choice of ligand, solvent, and halide additive. The resulting prenylated and reverse-prenylated products were transformed into ent-flustramides and ent-flustramines A and B. Additionally, control of the regio- and diastereoselectivity was obtained using pi-geranylpalladium complexes.
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